Toluene → 9-[Bis(4-methylphenyl)amino]phenyl-10-bromoanthracene

HRID 132509

Reaktionsgleichung

Reaktionsgleichung von HRID 132509
Br[C:2]1[C:3]2[C:8]([C:9]([Br:16])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([N:24](C2C=CC(B(O)O)=CC=2)[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1.[C:41]1(C)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C(O)C>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[C:2]2[C:3]3[C:8]([C:9]([Br:16])=[C:10]4[C:15]=2[C:14]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:22][CH:23]=1

Komponenten

9

Edukt 4

HCID 1140TolueneHCID 10340Sodium Carbonate2×HCID 682269,10-DibromoanthraceneHCID 23083792[4-[Bis(4-methylphenyl)amino]phenyl]boronic acid

Produkt 1

HCID 866013499-[Bis(4-methylphenyl)amino]phenyl-10-bromoanthracene

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a nitrogen flow, 1 g (2.98 mmol) of 9,10-dibromoanthracene and 1.44 g (4.46 mmol) of bis(4-methylphenyl)aminobenzene-4-boronic acid were dissolved and stirred in a deaerated mixture solvent of 100 ml of toluene and 50 ml of ethanol, followed by dropping a sodium carbonate aqueous solution prepared by dissolving 9 g of anhydrous sodium carbonate in 45 ml of water. After stirring the mixture for 30 minutes, 257 mg (0.223 mmol) of tetrakis(triphenylphosphine)palladium was added thereto. Then, the mixture was heated and stirred for about 3 hours in an oil bath heated at 80° C. After returning the reaction solution to room temperature, 40 ml of water and 50 ml of ethyl acetate were added thereto and the resultant solution was then separated into an aqueous layer and an organic layer. Furthermore, the aqueous layer was extracted with toluene and ethyl acetate, and was then combined with the previous organic layer and dried with magnesium sulfate. The solvent was evaporated and then the residue was purified by silicagel-column chromatography (toluene:hexane=1:2) to obtain 1.13 g of 9-[bis(4-methylphenyl)amino]phenyl-10-bromoanthracene.

Aufarbeitung

  1. customprepared
  2. temperatureThen, the mixture was heated
  3. stirringstirred for about 3 hours in an oil bath
  4. customto room temperature
  5. customthe resultant solution was then separated into an aqueous layer
  6. extractionFurthermore, the aqueous layer was extracted with toluene and ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silicagel-column chromatography (toluene:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-54ef8cedab1c4634807a5cf24457e021
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07387845B2

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